5-Tert-butyl-m-xylene → 4-tert-butyl-2,6-dimethylbenzenesulfonyl chloride

HRID 1925760Notes

Reaction equation

HRID 1925760 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][S:14](O)(=[O:16])=[O:15]>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([CH3:12])[C:8]([S:14]([Cl:13])(=[O:16])=[O:15])=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 73785-Tert-butyl-m-xyleneHCID 24638Chlorosulfonic acid

Product 1

HCID 38685064-tert-butyl-2,6-dimethylbenzenesulfonyl chlorideYield 19.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized as described for 1 using 1-tert-butyl-3,5-dimethylbenzene (5.76 mL; 30.81 mmol), chlorosulfonic acid (2.46 mL; 36.96 mmol) and anhydrous dichloromethane (200 mL). The crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 25% v/v gradient elution over 400 mL) to give the title compound as a white solid (1.60 g).

Workup

  1. customSynthesized
  2. customThe crude residue was purified by automated silica gel column chromatography (Biotage®)
  3. washeluting with ethyl acetate/hexanes (0 to 25% v/v gradient elution over 400 mL)

Sources & evidence

ORD record
ord-5a74a4b7dea942b0bbc17f178f9a9026
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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